NPASS Compound

Structure

NPC45037 OpenBabel07101719512D 75 79 0 0 1 0 0 0 0 0999 V2000 -7.1723 -0.9842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2142 -1.9579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2904 -3.3719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1948 -3.3719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6536 1.3370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2307 -3.9687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1186 -1.9579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4259 -6.1324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4259 -5.1572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4187 -6.6200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4187 -4.6697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2632 -6.1324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9343 3.9171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0080 5.2209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4596 0.3845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9554 -1.2276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1815 4.5371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2553 5.8409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3903 0.0934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8861 -1.5187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3019 0.2279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8489 0.6865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5151 -0.7236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5424 -0.1129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6003 3.6391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9522 -4.1821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8114 0.0151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3441 -2.3982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2485 -2.3982 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2394 0.9453 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2632 -5.1572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8475 4.2591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7421 -0.2760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3420 5.4989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6035 -0.8582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0193 0.8884 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6650 0.9453 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4398 2.6773 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9522 -3.2069 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5982 0.9666 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4458 -1.0147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9763 -0.8509 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4722 -1.8649 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7727 1.7617 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4321 -1.8649 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8061 1.8399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3621 2.3606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9903 -3.0464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6675 1.2577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5423 2.3606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9044 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7717 -2.5823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0805 -0.9718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6591 -1.9663 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.9500 0.5973 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.1316 1.7617 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4646 2.6773 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1327 -2.5823 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0553 2.4221 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.9140 -3.0464 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.8238 -0.9718 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5893 6.1189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5342 -1.1493 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3156 1.6271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1633 -0.3543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4333 -1.6609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5235 2.5004 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8262 3.2183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6737 -3.9687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4542 2.2093 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0782 3.2183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8762 0.0805 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3706 -3.3518 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8648 -1.2112 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 28 1 0 0 0 0 3 28 1 0 0 0 0 6 60 1 0 0 0 0 7 29 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 31 2 0 0 0 0 12 31 1 0 0 0 0 13 17 1 0 0 0 0 13 32 2 0 0 0 0 14 18 2 0 0 0 0 14 32 1 0 0 0 0 15 19 1 0 0 0 0 15 33 2 0 0 0 0 16 20 2 0 0 0 0 16 33 1 0 0 0 0 17 34 2 0 0 0 0 18 34 1 0 0 0 0 19 35 2 0 0 0 0 20 35 1 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 23 41 1 0 0 0 0 24 42 1 0 0 0 0 25 32 1 0 0 0 0 26 31 1 0 0 0 0 27 33 1 0 0 0 0 27 40 1 0 0 0 0 29 4 1 6 0 0 0 30 5 1 1 0 0 0 30 44 1 0 0 0 0 30 75 1 0 0 0 0 34 62 1 0 0 0 0 35 63 1 0 0 0 0 36 21 1 1 0 0 0 36 46 1 0 0 0 0 36 55 1 0 0 0 0 37 22 1 6 0 0 0 37 51 1 0 0 0 0 37 56 1 0 0 0 0 38 25 1 6 0 0 0 38 47 1 0 0 0 0 38 57 1 0 0 0 0 39 26 1 6 0 0 0 39 48 1 0 0 0 0 39 60 1 0 0 0 0 40 49 1 0 0 0 0 40 64 1 6 0 0 0 41 54 2 0 0 0 0 41 65 1 0 0 0 0 42 61 1 0 0 0 0 42 66 1 1 0 0 0 43 28 1 6 0 0 0 43 53 1 0 0 0 0 43 58 1 0 0 0 0 44 50 1 0 0 0 0 44 59 1 1 0 0 0 45 29 1 6 0 0 0 45 52 1 0 0 0 0 45 61 1 0 0 0 0 46 59 2 3 0 0 0 46 67 1 0 0 0 0 47 56 2 3 0 0 0 47 68 1 0 0 0 0 48 58 2 3 0 0 0 48 69 1 0 0 0 0 49 55 2 3 0 0 0 49 70 1 0 0 0 0 50 57 2 3 0 0 0 50 71 1 0 0 0 0 51 61 1 0 0 0 0 51 72 2 0 0 0 0 52 60 1 0 0 0 0 52 73 2 0 0 0 0 53 74 2 0 0 0 0 53 75 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1042.5
Volume:	1046.042
LogP:	0.938
LogD:	0.659
LogS:	-1.979
# Rotatable Bonds:	17
TPSA:	340.91
# H-Bond Aceptor:	22
# H-Bond Donor:	11
# Rings:	5
# Heavy Atoms:	22

MedChem Properties

QED Drug-Likeness Score:	0.055
Synthetic Accessibility Score:	7.218
Fsp3:	0.491
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.89
MDCK Permeability:	5.0154591008322313e-05
Pgp-inhibitor:	0.039
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.949
20% Bioavailability (F20%):	0.953
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.085
Plasma Protein Binding (PPB):	62.90863800048828%
Volume Distribution (VD):	0.429
Pgp-substrate:	20.53415298461914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.065
CYP2C19-substrate:	0.036
CYP2C9-inhibitor:	0.262
CYP2C9-substrate:	0.794
CYP2D6-inhibitor:	0.033
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.188
CYP3A4-substrate:	0.043

ADMET: Excretion

Clearance (CL):	1.247
Half-life (T1/2):	0.848

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.997
Drug-inuced Liver Injury (DILI):	0.985
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.789
Maximum Recommended Daily Dose:	0.976
Skin Sensitization:	0.481
Carcinogencity:	0.166
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.582

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC45037

Natural Product ID:	NPC45037
*Common Name:**	Rel-(S)-N1-((2S,5S,8S,11R,12S,15S,18S,21R)-5-Benzyl-2-Sec-Butyl-21-Hydroxy-15-(4-Hydroxybenzyl)-8-Isopropyl-4,11-Dimethyl-3,6,9,13,16,22-Hexaoxo-10-Oxa-1,4,7,14,17-Pentaazabicyclo[16.3.1]Docosan-12-Yl)-2-((R)-2-Hydroxy-3-(4-Hydroxyphenyl)Propanamido)Pentanediamide
IUPAC Name:	(2S)-N-[(2S,5S,8S,11R,12S,15S,18S,21R)-5-benzyl-2-[(2R)-butan-2-yl]-21-hydroxy-15-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-8-propan-2-yl-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]-2-[[(2R)-2-hydroxy-3-(4-hydroxyphenyl)propanoyl]amino]pentanediamide
Synonyms:
Standard InCHIKey:	JRUSMDKOMMRBPY-RILALQOVSA-N
Standard InCHI:	InChI=1S/C53H70N8O14/c1-7-29(4)45-52(73)60(6)39(26-31-11-9-8-10-12-31)48(69)58-43(28(2)3)53(74)75-30(5)44(59-46(67)36(21-23-41(54)65)55-49(70)40(64)27-33-15-19-35(63)20-16-33)50(71)57-38(25-32-13-17-34(62)18-14-32)47(68)56-37-22-24-42(66)61(45)51(37)72/h8-20,28-30,36-40,42-45,62-64,66H,7,21-27H2,1-6H3,(H2,54,65)(H,55,70)(H,56,68)(H,57,71)(H,58,69)(H,59,67)/t29-,30-,36+,37+,38+,39+,40-,42-,43+,44+,45+/m1/s1
SMILES:	CC[C@H]([C@@H]1N2[C@H](O)CC[C@@H](C2=O)N=C(O)[C@H](Cc2ccc(cc2)O)N=C(O)[C@H]([C@H](OC(=O)[C@@H](N=C([C@@H](N(C1=O)C)Cc1ccccc1)O)C(C)C)C)N=C([C@@H](N=C([C@@H](Cc1ccc(cc1)O)O)O)CCC(=N)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2011684
PubChem CID:	70691538
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11000050]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11374973]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Einan Reservoir in Israel	n.a.	PMID[12141855]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12141855]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18163584]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18558743]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18973386]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	water bloom of the cyanobacterium Microcystis aeruginosa	n.a.	n.a.	PMID[19650639]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	bloom material	Lake Kinneret, Israel	n.a.	PMID[22280481]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Kibbutz Geva, Israel	n.a.	PMID[23153007]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Water Reservoir near Kibbutz Hafetz Haim, Israel	n.a.	PMID[23718637]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	Bloom	n.a.	n.a.	PMID[24261937]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24642434]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24868986]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29405714]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	Bloom	n.a.	n.a.	PMID[29847132]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9249979]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9842728]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	Database[Title]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	260.0	nM	PMID[496738]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC45037 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	997
0.2-0.3	3902
0.3-0.4	13118
0.4-0.5	11099
0.5-0.6	11961
0.6-0.7	1024
0.7-0.8	317
0.8-0.85	38
0.85-0.9	25
0.9-0.95	21
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9748	High Similarity	NPC273755
0.9686	High Similarity	NPC230611
0.9627	High Similarity	NPC50016
0.9565	High Similarity	NPC473402
0.9503	High Similarity	NPC306804
0.9444	High Similarity	NPC155506
0.9444	High Similarity	NPC473354
0.9444	High Similarity	NPC159767
0.9398	High Similarity	NPC294951
0.9375	High Similarity	NPC294516
0.9375	High Similarity	NPC107938
0.9337	High Similarity	NPC471526
0.9273	High Similarity	NPC269750
0.9273	High Similarity	NPC194671
0.9259	High Similarity	NPC46009
0.9162	High Similarity	NPC476321
0.9146	High Similarity	NPC137627
0.9141	High Similarity	NPC475204
0.9141	High Similarity	NPC475123
0.9141	High Similarity	NPC40234
0.9123	High Similarity	NPC473305
0.9123	High Similarity	NPC163961
0.9091	High Similarity	NPC471165
0.9091	High Similarity	NPC279871
0.9091	High Similarity	NPC476227
0.8976	High Similarity	NPC26108
0.896	High Similarity	NPC473407
0.896	High Similarity	NPC473378
0.8916	High Similarity	NPC248670
0.8857	High Similarity	NPC302715
0.883	High Similarity	NPC471048
0.883	High Similarity	NPC471050
0.883	High Similarity	NPC471049
0.8824	High Similarity	NPC473404
0.8814	High Similarity	NPC471592
0.8736	High Similarity	NPC102959
0.8686	High Similarity	NPC60516
0.8686	High Similarity	NPC61332
0.8686	High Similarity	NPC240130
0.8644	High Similarity	NPC65714
0.8631	High Similarity	NPC89831
0.8554	High Similarity	NPC63931
0.8547	High Similarity	NPC473371
0.8529	High Similarity	NPC158277
0.8344	Intermediate Similarity	NPC473341
0.8284	Intermediate Similarity	NPC61004
0.8263	Intermediate Similarity	NPC471527
0.8261	Intermediate Similarity	NPC469443
0.8261	Intermediate Similarity	NPC477551
0.8251	Intermediate Similarity	NPC477552
0.8251	Intermediate Similarity	NPC477550
0.8235	Intermediate Similarity	NPC328649
0.8204	Intermediate Similarity	NPC244336
0.8171	Intermediate Similarity	NPC233702
0.8161	Intermediate Similarity	NPC196243
0.8156	Intermediate Similarity	NPC94862
0.8133	Intermediate Similarity	NPC476268
0.8129	Intermediate Similarity	NPC302597
0.8125	Intermediate Similarity	NPC91953
0.8122	Intermediate Similarity	NPC248822
0.8121	Intermediate Similarity	NPC262166
0.8121	Intermediate Similarity	NPC122590
0.8118	Intermediate Similarity	NPC223207
0.8113	Intermediate Similarity	NPC239762
0.8113	Intermediate Similarity	NPC163392
0.8092	Intermediate Similarity	NPC328494
0.8086	Intermediate Similarity	NPC81026
0.807	Intermediate Similarity	NPC471771
0.807	Intermediate Similarity	NPC304074
0.807	Intermediate Similarity	NPC290755
0.8063	Intermediate Similarity	NPC197921
0.8059	Intermediate Similarity	NPC471051
0.8059	Intermediate Similarity	NPC471053
0.8059	Intermediate Similarity	NPC471052
0.8054	Intermediate Similarity	NPC323662
0.8035	Intermediate Similarity	NPC198254
0.8035	Intermediate Similarity	NPC274198
0.8025	Intermediate Similarity	NPC266741
0.8024	Intermediate Similarity	NPC244509
0.8012	Intermediate Similarity	NPC469360
0.8	Intermediate Similarity	NPC220060
0.8	Intermediate Similarity	NPC473491
0.7988	Intermediate Similarity	NPC62104
0.7988	Intermediate Similarity	NPC1390
0.7978	Intermediate Similarity	NPC477637
0.7968	Intermediate Similarity	NPC242728
0.7967	Intermediate Similarity	NPC64140
0.7967	Intermediate Similarity	NPC174122
0.7964	Intermediate Similarity	NPC39431
0.7958	Intermediate Similarity	NPC469444
0.7944	Intermediate Similarity	NPC138083
0.7941	Intermediate Similarity	NPC469243
0.7939	Intermediate Similarity	NPC2501
0.7935	Intermediate Similarity	NPC328763
0.7931	Intermediate Similarity	NPC196091
0.7931	Intermediate Similarity	NPC471568
0.7931	Intermediate Similarity	NPC473693
0.7931	Intermediate Similarity	NPC276506
0.7927	Intermediate Similarity	NPC16188
0.7919	Intermediate Similarity	NPC141957
0.7912	Intermediate Similarity	NPC234069
0.7907	Intermediate Similarity	NPC472923
0.7904	Intermediate Similarity	NPC202198
0.7904	Intermediate Similarity	NPC56685
0.7898	Intermediate Similarity	NPC136797
0.7875	Intermediate Similarity	NPC6570
0.7875	Intermediate Similarity	NPC127741
0.7874	Intermediate Similarity	NPC280022
0.7874	Intermediate Similarity	NPC186617
0.7872	Intermediate Similarity	NPC473450
0.7865	Intermediate Similarity	NPC97526
0.7865	Intermediate Similarity	NPC119652
0.7861	Intermediate Similarity	NPC50548
0.784	Intermediate Similarity	NPC476989
0.7838	Intermediate Similarity	NPC314083
0.7836	Intermediate Similarity	NPC475544
0.7835	Intermediate Similarity	NPC469445
0.7816	Intermediate Similarity	NPC209463
0.7812	Intermediate Similarity	NPC219350
0.7812	Intermediate Similarity	NPC194699
0.7807	Intermediate Similarity	NPC144314
0.7803	Intermediate Similarity	NPC217804
0.7803	Intermediate Similarity	NPC210377
0.7803	Intermediate Similarity	NPC5719
0.7803	Intermediate Similarity	NPC22883
0.7798	Intermediate Similarity	NPC5194
0.7798	Intermediate Similarity	NPC261934
0.7796	Intermediate Similarity	NPC477632
0.7796	Intermediate Similarity	NPC477638
0.7791	Intermediate Similarity	NPC241794
0.7754	Intermediate Similarity	NPC149962
0.7747	Intermediate Similarity	NPC315542
0.7744	Intermediate Similarity	NPC52748
0.7722	Intermediate Similarity	NPC32064
0.7719	Intermediate Similarity	NPC56635
0.7714	Intermediate Similarity	NPC63040
0.7706	Intermediate Similarity	NPC473580
0.7705	Intermediate Similarity	NPC276120
0.7697	Intermediate Similarity	NPC477462
0.7667	Intermediate Similarity	NPC475421
0.7657	Intermediate Similarity	NPC254700
0.7657	Intermediate Similarity	NPC15068
0.7653	Intermediate Similarity	NPC277306
0.7653	Intermediate Similarity	NPC469442
0.765	Intermediate Similarity	NPC299806
0.764	Intermediate Similarity	NPC475532
0.7632	Intermediate Similarity	NPC123859
0.7624	Intermediate Similarity	NPC153554
0.7616	Intermediate Similarity	NPC297145
0.7616	Intermediate Similarity	NPC323336
0.7616	Intermediate Similarity	NPC197743
0.7616	Intermediate Similarity	NPC326349
0.7598	Intermediate Similarity	NPC17698
0.7598	Intermediate Similarity	NPC165285
0.7598	Intermediate Similarity	NPC164608
0.7581	Intermediate Similarity	NPC29531
0.7576	Intermediate Similarity	NPC25539
0.7572	Intermediate Similarity	NPC319320
0.7572	Intermediate Similarity	NPC287757
0.756	Intermediate Similarity	NPC471821
0.756	Intermediate Similarity	NPC471820
0.7541	Intermediate Similarity	NPC167763
0.7541	Intermediate Similarity	NPC470112
0.7541	Intermediate Similarity	NPC470903
0.7516	Intermediate Similarity	NPC326966
0.7516	Intermediate Similarity	NPC257390
0.75	Intermediate Similarity	NPC135121
0.75	Intermediate Similarity	NPC478005
0.75	Intermediate Similarity	NPC477631
0.7487	Intermediate Similarity	NPC326027
0.7487	Intermediate Similarity	NPC477636
0.7485	Intermediate Similarity	NPC201244
0.7485	Intermediate Similarity	NPC477217
0.7475	Intermediate Similarity	NPC326333
0.7472	Intermediate Similarity	NPC129486
0.7471	Intermediate Similarity	NPC7817
0.7471	Intermediate Similarity	NPC475168
0.7469	Intermediate Similarity	NPC244866
0.7447	Intermediate Similarity	NPC477526
0.7443	Intermediate Similarity	NPC133470
0.7443	Intermediate Similarity	NPC289776
0.7443	Intermediate Similarity	NPC191863
0.7442	Intermediate Similarity	NPC470902
0.744	Intermediate Similarity	NPC262077
0.7439	Intermediate Similarity	NPC68865
0.7439	Intermediate Similarity	NPC64205
0.7438	Intermediate Similarity	NPC478007
0.7432	Intermediate Similarity	NPC170302
0.7432	Intermediate Similarity	NPC475564
0.7432	Intermediate Similarity	NPC475409
0.7427	Intermediate Similarity	NPC476744
0.7423	Intermediate Similarity	NPC311357
0.7421	Intermediate Similarity	NPC471563
0.7416	Intermediate Similarity	NPC473502
0.7382	Intermediate Similarity	NPC329295
0.7382	Intermediate Similarity	NPC477639
0.7368	Intermediate Similarity	NPC476743
0.7366	Intermediate Similarity	NPC478008
0.7365	Intermediate Similarity	NPC161069
0.7365	Intermediate Similarity	NPC176226

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC45037 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	121
0.1-0.2	384
0.2-0.3	803
0.3-0.4	1861
0.4-0.5	3051
0.5-0.6	2334
0.6-0.7	575
0.7-0.8	21
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7929	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD7608	Discontinued
0.7778	Intermediate Similarity	NPD8019	Approved
0.7759	Intermediate Similarity	NPD8303	Discontinued
0.7539	Intermediate Similarity	NPD7810	Phase 3
0.7539	Intermediate Similarity	NPD7811	Phase 3
0.75	Intermediate Similarity	NPD8323	Discontinued
0.7472	Intermediate Similarity	NPD7485	Phase 3
0.7472	Intermediate Similarity	NPD7484	Phase 3
0.747	Intermediate Similarity	NPD7978	Discontinued
0.7453	Intermediate Similarity	NPD3136	Phase 2
0.741	Intermediate Similarity	NPD7450	Phase 2
0.7384	Intermediate Similarity	NPD7131	Phase 3
0.7371	Intermediate Similarity	NPD7495	Discontinued
0.7303	Intermediate Similarity	NPD8031	Discontinued
0.7273	Intermediate Similarity	NPD6853	Approved
0.7273	Intermediate Similarity	NPD5946	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6851	Approved
0.7225	Intermediate Similarity	NPD7303	Discontinued
0.7152	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6681	Discovery
0.7104	Intermediate Similarity	NPD5137	Approved
0.7086	Intermediate Similarity	NPD7523	Phase 3
0.7081	Intermediate Similarity	NPD4659	Approved
0.7074	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD8417	Discontinued
0.7059	Intermediate Similarity	NPD6297	Approved
0.7045	Intermediate Similarity	NPD8315	Phase 1
0.7041	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD2098	Approved
0.7006	Intermediate Similarity	NPD6346	Approved
0.6977	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4652	Approved
0.6951	Remote Similarity	NPD7451	Discontinued
0.6939	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3125	Approved
0.6932	Remote Similarity	NPD7613	Discontinued
0.6923	Remote Similarity	NPD8173	Phase 2
0.6923	Remote Similarity	NPD8172	Phase 2
0.6919	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD2097	Approved
0.6902	Remote Similarity	NPD2017	Approved
0.6902	Remote Similarity	NPD2890	Approved
0.6902	Remote Similarity	NPD2889	Approved
0.6902	Remote Similarity	NPD2888	Approved
0.689	Remote Similarity	NPD4103	Phase 2
0.689	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD1330	Phase 2
0.6885	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3536	Discontinued
0.6872	Remote Similarity	NPD8356	Approved
0.6845	Remote Similarity	NPD5745	Approved
0.6839	Remote Similarity	NPD3400	Discontinued
0.6839	Remote Similarity	NPD6676	Phase 2
0.6839	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD8430	Approved
0.681	Remote Similarity	NPD2562	Approved
0.681	Remote Similarity	NPD2561	Approved
0.6796	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD3552	Approved
0.6784	Remote Similarity	NPD3553	Approved
0.6784	Remote Similarity	NPD3555	Approved
0.6784	Remote Similarity	NPD3554	Approved
0.6782	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD8351	Phase 2
0.6763	Remote Similarity	NPD8076	Discontinued
0.6758	Remote Similarity	NPD7972	Discontinued
0.6758	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5218	Approved
0.6739	Remote Similarity	NPD5219	Approved
0.6739	Remote Similarity	NPD8070	Approved
0.6737	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5746	Approved
0.6725	Remote Similarity	NPD6073	Approved
0.6725	Remote Similarity	NPD5314	Approved
0.6725	Remote Similarity	NPD2568	Approved
0.6723	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD8161	Suspended
0.6706	Remote Similarity	NPD5120	Approved
0.6706	Remote Similarity	NPD5121	Approved
0.6706	Remote Similarity	NPD5119	Approved
0.6702	Remote Similarity	NPD5445	Approved
0.6686	Remote Similarity	NPD6294	Approved
0.6686	Remote Similarity	NPD6852	Discontinued
0.6686	Remote Similarity	NPD6295	Approved
0.6684	Remote Similarity	NPD42	Phase 2
0.6684	Remote Similarity	NPD6042	Phase 2
0.6684	Remote Similarity	NPD7617	Discontinued
0.6683	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5201	Approved
0.6667	Remote Similarity	NPD555	Phase 2
0.6667	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4617	Approved
0.6667	Remote Similarity	NPD4620	Approved
0.6667	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5203	Approved
0.665	Remote Similarity	NPD7585	Approved
0.6649	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD4521	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6072	Discontinued
0.6648	Remote Similarity	NPD6677	Suspended
0.6648	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7715	Approved
0.6647	Remote Similarity	NPD7714	Approved
0.6647	Remote Similarity	NPD6405	Approved
0.6647	Remote Similarity	NPD6407	Approved
0.6633	Remote Similarity	NPD8025	Phase 2
0.663	Remote Similarity	NPD3455	Phase 2
0.663	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD3052	Approved
0.6628	Remote Similarity	NPD3054	Approved
0.6627	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD3061	Approved
0.6608	Remote Similarity	NPD5296	Approved
0.6608	Remote Similarity	NPD3059	Approved
0.6608	Remote Similarity	NPD8265	Approved
0.6608	Remote Similarity	NPD3062	Approved
0.6607	Remote Similarity	NPD4177	Approved
0.6607	Remote Similarity	NPD4175	Approved
0.6606	Remote Similarity	NPD2584	Suspended
0.6602	Remote Similarity	NPD7583	Approved
0.6584	Remote Similarity	NPD7565	Approved
0.6576	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD5773	Approved
0.6576	Remote Similarity	NPD5772	Approved
0.6575	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7554	Discontinued
0.6573	Remote Similarity	NPD6667	Approved
0.6573	Remote Similarity	NPD6666	Approved
0.6569	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD8162	Phase 2
0.6566	Remote Similarity	NPD4677	Discontinued
0.6562	Remote Similarity	NPD5190	Phase 2
0.6562	Remote Similarity	NPD5557	Phase 1
0.6557	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD6390	Discontinued
0.6552	Remote Similarity	NPD1753	Discontinued
0.655	Remote Similarity	NPD259	Phase 1
0.6548	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6107	Approved
0.6541	Remote Similarity	NPD5967	Approved
0.6541	Remote Similarity	NPD7737	Approved
0.6541	Remote Similarity	NPD7738	Approved
0.6536	Remote Similarity	NPD7213	Phase 3
0.6536	Remote Similarity	NPD6088	Approved
0.6536	Remote Similarity	NPD7212	Phase 2
0.6532	Remote Similarity	NPD823	Approved
0.6532	Remote Similarity	NPD5725	Approved
0.6532	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD817	Approved
0.6527	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD5723	Approved
0.6522	Remote Similarity	NPD5356	Approved
0.6522	Remote Similarity	NPD7011	Discontinued
0.6522	Remote Similarity	NPD5355	Approved
0.6515	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD2239	Approved
0.6514	Remote Similarity	NPD2240	Approved
0.6514	Remote Similarity	NPD9570	Approved
0.6513	Remote Similarity	NPD5035	Approved
0.6513	Remote Similarity	NPD7281	Phase 3
0.6513	Remote Similarity	NPD7280	Phase 3
0.6512	Remote Similarity	NPD826	Approved
0.6512	Remote Similarity	NPD6623	Phase 3
0.6512	Remote Similarity	NPD825	Approved
0.651	Remote Similarity	NPD4603	Phase 2
0.6503	Remote Similarity	NPD2218	Phase 2
0.6503	Remote Similarity	NPD2217	Approved
0.65	Remote Similarity	NPD6419	Discontinued
0.65	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3985	Discontinued
0.65	Remote Similarity	NPD7447	Phase 1
0.6497	Remote Similarity	NPD5037	Approved
0.6497	Remote Similarity	NPD5038	Approved
0.6495	Remote Similarity	NPD7039	Approved
0.6495	Remote Similarity	NPD7038	Approved
0.6491	Remote Similarity	NPD601	Approved
0.6491	Remote Similarity	NPD597	Approved
0.6491	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4619	Approved
0.6491	Remote Similarity	NPD4621	Approved
0.6491	Remote Similarity	NPD598	Approved
0.6489	Remote Similarity	NPD2904	Discontinued
0.6489	Remote Similarity	NPD5823	Approved
0.6488	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD6863	Phase 2
0.6486	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6556	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data